Synthesis of tricyclic systems on the basis of σ-adduct of 3,5-dinitropyridin-2-ol with acetone

Иванова, Е. В.; Blokhin, I. V.; Fedyanin, Ivan V.; Shakhkel'dyan, I. V.; Atroshchenko, Yu. M.

doi:10.1134/s1070428015040065

Russ J Org Chem

2015

DOI: 10.1134/s1070428015040065

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Synthesis of tricyclic systems on the basis of σ-adduct of 3,5-dinitropyridin-2-ol with acetone

Е. В. Иванова

I. V. Blokhin

Ivan V. Fedyanin

et al.

Abstract: A series of new 4, 8-dinitro-2,6-diazatricyclo[6.4.0.0 4,9 ]dodecane-3,11-dione derivatives have been synthesized by the Mannich reaction of primary amines with formaldehyde and Janovsky complex of 3,5-dinitropyridin-2-ol with acetone.

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Cited by 3 publications

References 12 publications

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Dinitropyridines: Synthesis and Reactions

Starosotnikov,

Bastrakov

2024

Asian J Org Chem

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Dinitropyridines are one of the promising classes of heterocyclic compounds. They are considered as useful precursors of explosives and energetic compounds, agrochemicals, biosensors and biologically active compounds with diverse properties: antitumor, antiviral, anti‐neurodegenerative. Preliminary analysis of literature data shows that the chemistry of polynitropyridines has been actively developing over the past few decades. This is evidenced by the steadily growing annual number of publications. In this review the literature on the synthesis, reactions and practical application of isomeric dinitropyridines over a period of 2010‐2024 is analyzed.

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Dinitropyridines: Synthesis and Reactions

Starosotnikov,

Bastrakov

2024

Asian J Org Chem

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Synthesis of New 10-R-1,8-Dinitro-3-oxa-5,10-diazatricyclo-[6.3.1.02,6]dodeca-2(6),4-diene Derivatives

et al. 2018

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Synthesis of 3-R-1,5-DINITRO-3-AZABICYCLO[3.3.1]NON-7-EN-6-IMINES Based on 2,4-Dinitroaniline

Mukhtorov,

Aleksandrov,

Simonov

et al. 2024

tnusns

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We have synthesized new derivatives of 3-azabicyclo[3.3.1]nonane by Mannich condensation of the hydride σ-adduct of 2,4-dinitroaniline with formaldehyde and primary amines. The synthesis is carried out in two stages. In the first stage, the action of potassium tetrahydroborate (KBH4) on a solution of 2,4-dinitroaniline resulted in the reduction of the C=C bond of the aromatic ring with the formation of a two-charged hydride diadduct. The obtained diadduct without isolation from the solution and under ice cooling was introduced into the Mannich condensation reaction with formaldehyde and primary amine solution. When the reaction mixture is acidified with dilute phosphoric acid to pH 4÷5, the target products are crystallized. After recrystallization from acetone, the yield of target products, depending on the substituent at the nitrogen atom, was 65–70%. This method of obtaining is characterized by relative simplicity, the availability of reagents that makes it possible to carry out reaction under a mild acidic condition to 3-azabicyclo[3.3.1]nonane derivatives containing nitro groups that are promising from the point of view of further functionalization. The structure of the obtained compounds was proved by IR, 1H-, 13C-, two-dimensional correlation NMR spectroscopy, as well as high-resolution mass spectrometry (HRMS) data.

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Synthesis of tricyclic systems on the basis of σ-adduct of 3,5-dinitropyridin-2-ol with acetone

Abstract: A series of new 4, 8-dinitro-2,6-diazatricyclo[6.4.0.0 4,9 ]dodecane-3,11-dione derivatives have been synthesized by the Mannich reaction of primary amines with formaldehyde and Janovsky complex of 3,5-dinitropyridin-2-ol with acetone.

Cited by 3 publications

References 12 publications

Dinitropyridines: Synthesis and Reactions

Dinitropyridines: Synthesis and Reactions

Synthesis of New 10-R-1,8-Dinitro-3-oxa-5,10-diazatricyclo-[6.3.1.02,6]dodeca-2(6),4-diene Derivatives

Synthesis of 3-R-1,5-DINITRO-3-AZABICYCLO[3.3.1]NON-7-EN-6-IMINES Based on 2,4-Dinitroaniline

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